Namitecan

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 206589

CAS#: 372105-27-6

Description: Namitecan, also known as ST-1968, is a new water-soluble camptothecin analogue which showed high antitumor activity in preclinical models. ST1968 exhibited an impressive activity against several tumors including models of ovarian and colon carcinoma in which a high rate of cures was observed. t ST1968 was able to overcome the most relevant mechanisms associated with the development of topotecan resistance (i.e., slow proliferation and target downregulation) owing to its peculiar pharmacokinetic behaviour.


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Namitecan is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206589
Name: Namitecan
CAS#: 372105-27-6
Chemical Formula: C23H22N4O5
Exact Mass: 434.159
Molecular Weight: 434.452
Elemental Analysis: C, 63.59; H, 5.10; N, 12.90; O, 18.41


Synonym: ST-1968; ST 1968; ST1968; Namitecan.

IUPAC/Chemical Name: (4S)-11-((E)-((2-Aminoethoxy)imino)methyl)-4-ethyl-4-hydroxy-1,12-dihydro-14H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H)-dione

InChi Key: IBTISPLPBBHVSU-UVOOVGFISA-N

InChi Code: InChI=1S/C23H22N4O5/c1-2-23(30)17-9-19-20-15(11-27(19)21(28)16(17)12-31-22(23)29)14(10-25-32-8-7-24)13-5-3-4-6-18(13)26-20/h3-6,9-10,30H,2,7-8,11-12,24H2,1H3/b25-10+/t23-/m0/s1

SMILES Code: O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=C(/C=N/OCCN)C5=CC=CC=C5N=C4C3=C2)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Joerger M, Hess D, Delmonte A, Gallerani E, Barbieri P, Pace S, Sessa C. Phase-I dose finding and pharmacokinetic study of the novel hydrophilic camptothecin ST-1968 (namitecan) in patients with solid tumors. Invest New Drugs. 2015 Apr;33(2):472-9. doi: 10.1007/s10637-015-0219-5. Epub 2015 Feb 20. PubMed PMID: 25693886.

2: Joerger M, Hess D, Delmonte A, Gallerani E, Fasolo A, Gianni L, Cresta S, Barbieri P, Pace S, Sessa C. Integrative population pharmacokinetic and pharmacodynamic dose finding approach of the new camptothecin compound namitecan (ST1968). Br J Clin Pharmacol. 2015 Jul;80(1):128-38. doi: 10.1111/bcp.12583. Epub 2015 Jun 3. PubMed PMID: 25580946; PubMed Central PMCID: PMC4500332.

3: De Cesare M, Lauricella C, Veronese SM, Cominetti D, Pisano C, Zunino F, Zaffaroni N, Zuco V. Synergistic antitumor activity of cetuximab and namitecan in human squamous cell carcinoma models relies on cooperative inhibition of EGFR expression and depends on high EGFR gene copy number. Clin Cancer Res. 2014 Feb 15;20(4):995-1006. doi: 10.1158/1078-0432.CCR-13-1684. Epub 2013 Dec 10. PubMed PMID: 24327272.

4: Meco D, Di Francesco AM, Cusano G, Bucci F, Pierri F, Patriarca V, Torella AR, Pisano C, Riccardi R. Preclinical evaluation of the novel 7-substituted camptothecin Namitecan (ST1968) in paediatric tumour models. Cancer Chemother Pharmacol. 2012 Dec;70(6):811-22. doi: 10.1007/s00280-012-1973-0. Epub 2012 Sep 25. PubMed PMID: 23007316.

5: Beretta GL, Zuco V, De Cesare M, Perego P, Zaffaroni N. Namitecan: a hydrophilic camptothecin with a promising preclinical profile. Curr Med Chem. 2012;19(21):3488-501. Review. PubMed PMID: 22680917.

6: Cassinelli G, Zuco V, Petrangolini G, De Cesare M, Tortoreto M, Lanzi C, Cominetti D, Zaffaroni N, Orlandi A, Passeri D, Meco D, Di Francesco AM, Riccardi R, Bucci F, Pisano C, Zunino F. The curative efficacy of namitecan (ST1968) in preclinical models of pediatric sarcoma is associated with antiangiogenic effects. Biochem Pharmacol. 2012 Jul 15;84(2):163-71. doi: 10.1016/j.bcp.2012.04.005. Epub 2012 Apr 13. PubMed PMID: 22525722.

7: Dal Pozzo A, Esposito E, Ni M, Muzi L, Pisano C, Bucci F, Vesci L, Castorina M, Penco S. Conjugates of a novel 7-substituted camptothecin with RGD-peptides as α(v)β₃ integrin ligands: An approach to tumor-targeted therapy. Bioconjug Chem. 2010 Nov 17;21(11):1956-67. doi: 10.1021/bc100097r. Epub 2010 Oct 15. PubMed PMID: 20949910.

8: Zuco V, Benedetti V, Zunino F. ATM- and ATR-mediated response to DNA damage induced by a novel camptothecin, ST1968. Cancer Lett. 2010 Jun 28;292(2):186-96. doi: 10.1016/j.canlet.2009.12.001. Epub 2009 Dec 29. PubMed PMID: 20042274.

9: Badaloni E, Cabri W, Ciogli A, D'Acquarica I, Deias R, Gasparrini F, Giorgi F, Kotoni D, Villani C. Extending the use of "Inverted Chirality Columns Approach" for enantiomeric excess determination in absence of reference samples: Application to a water-soluble camptothecin derivative. J Chromatogr A. 2010 Feb 12;1217(7):1024-32. doi: 10.1016/j.chroma.2009.10.035. Epub 2009 Oct 17. PubMed PMID: 19863967.

10: Zuco V, Supino R, Favini E, Tortoreto M, Cincinelli R, Croce AC, Bucci F, Pisano C, Zunino F. Efficacy of ST1968 (namitecan) on a topotecan-resistant squamous cell carcinoma. Biochem Pharmacol. 2010 Feb 15;79(4):535-41. doi: 10.1016/j.bcp.2009.09.012. Epub . PubMed PMID: 19765546.

11: Pisano C, De Cesare M, Beretta GL, Zuco V, Pratesi G, Penco S, Vesci L, Foderà R, Ferrara FF, Guglielmi MB, Carminati P, Dallavalle S, Morini G, Merlini L, Orlandi A, Zunino F. Preclinical profile of antitumor activity of a novel hydrophilic camptothecin, ST1968. Mol Cancer Ther. 2008 Jul;7(7):2051-9. doi: 10.1158/1535-7163.MCT-08-0266. PubMed PMID: 18645015.

12: Pisano C, Zuco V, De Cesare M, Benedetti V, Vesci L, Foderà R, Bucci F, Aulicino C, Penco S, Carminati P, Zunino F. Intracellular accumulation and DNA damage persistence as determinants of human squamous cell carcinoma hypersensitivity to the novel camptothecin ST1968. Eur J Cancer. 2008 Jun;44(9):1332-40. doi: 10.1016/j.ejca.2008.04.004. Epub 2008 Apr 27. PubMed PMID: 18445521.

13: De Cesare M, Beretta GL, Tinelli S, Benedetti V, Pratesi G, Penco S, Dallavalle S, Merlini L, Pisano C, Carminati P, Zunino F. Preclinical efficacy of ST1976, a novel camptothecin analog of the 7-oxyiminomethyl series. Biochem Pharmacol. 2007 Mar 1;73(5):656-64. Epub 2006 Nov 9. PubMed PMID: 17169332.